反応 #44497

反応方程式

3-Bromo-2-bromomethyl-propionic acid methyl ester

1-cyclohex-1-enyl-pyrrolidine

triethyl amine

acetic acid

→

title compound

9-Oxo-bicyclo[3.3.1]nonane-3-carboxylic acid methyl ester

溶媒

CH3CN

water

反応条件

後処理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.ADDITIONwere added
3. 3
   温度Then, heating
4. 4
   その他The solvent was evaporated
5. 5
   その他the residue was partitioned with diethyl ether and water
6. 6
   洗浄The organic phase was washed with a NaHCO3 solution until the washes
7. 7
   その他It was then dried
8. 8
   ろ過filtered
9. 9
   その他evaporated
10. 10
    その他The residue was purified over silica gel using 2-30% diethyl ether in hexanes

実験手順

3-Bromo-2-bromomethyl-propionic acid methyl ester (30 g, 115 mmol) was added to a stirred solution of freshly distilled 1-cyclohex-1-enyl-pyrrolidine (20.4 mL, 126 mmol) and triethyl amine (35 mL, 252 mmol) in dry CH3CN (400 mL). After the addition, the mixture was heated (100° C.) and stirred for twelve hours before acetic acid (20 mL) and water (100 mL) were added. Then, heating was continued for another three hours. The solvent was evaporated and the residue was partitioned with diethyl ether and water. The organic phase was washed with a NaHCO3 solution until the washes became basic. It was then dried, filtered, and evaporated. The residue was purified over silica gel using 2-30% diethyl ether in hexanes to give the title compound as a clear oil.

出典